Record Information
Version1.0
Creation Date2009-06-18 20:15:07 UTC
Update Date2026-03-31 16:57:33 UTC
Accession NumberCHEM000899
Identification
Common NameAvermectin B1b
ClassSmall Molecule
DescriptionThe avermectins are a series of macrocyclic lactone derivatives with potent anthelmintic properties. A commonly used therapy in recent times has been based on oral or parenteral administration of avermectins, which are macrocyclic lactones produced by fermentation of various, carefully prepared laboratory broths using the soil micro-organism Streptomyces avermitilis. They show activity against a broad range of nematodes and arthropod parasites of domestic animals at dose rates of 300 microgram/kg or less. Unlike the macrolide or polyene antibiotics, they lack significant antibacterial or antifungal activity. (1)
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Avermectin
  • Bacterial Toxin
  • Ester
  • Ether
  • Lachrymator
  • Natural Compound
  • Organic Compound
  • Pesticide
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC47H70O14
Average Molecular Mass859.063 g/mol
Monoisotopic Mass858.477 g/mol
CAS Registry Number65195-56-4
IUPAC Name(10'E,14'E)-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11',13',22'-tetramethyl-6-(propan-2-yl)-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
Traditional Name(10'E,14'E)-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-6-isopropyl-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
SMILES[H]\C1=C(C)/C(OC2CC(OC)C(OC3CC(OC)C(O)C(C)O3)C(C)O2)C(C)\C([H])=C(/[H])\C(\[H])=C2/COC3C(O)C(C)=CC(C(=O)OC4CC(C1)OC1(C4)OC(C(C)C)C(C)C=C1)C23O
InChI IdentifierInChI=1S/C47H70O14/c1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h11-14,16-18,24-25,27,29-30,32-44,48-49,51H,15,19-23H2,1-10H3/b12-11+,26-14+,31-13+
InChI KeyZFUKERYTFURFGA-VOPGCZCJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Ketal
  • Pyran
  • Oxane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP3.91ALOGPS
logP5.4ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area170.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity226.58 m³·mol⁻¹ChemAxon
Polarizability92.91 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-107j-6300092280-4778382e0a01eeeb8c28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4j-6920081110-d46d86cdb9a071687560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9630110010-c43f6d4d793367845caaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3220041290-5d5adfa3fc3b84d98014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0296-1300091320-22d43a052cd64938a8d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ne-7700391010-0f66958cea11499c1e91Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityIt has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. (3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesActive ingredient in some commercial ant bait traps. (1)
Minimum Risk LevelNot Available
Health EffectsAvermectins are neurotoxic and have reproductive and developmental effects. (2)
SymptomsAvermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses. (2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID12960425
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available